Many researchers have explored language learning investment since Norton Peirce (1995) introduced the concept. However, most investment studies have recruited participants through language classes, which presupposes participant investment in formal learning. The current study went outside the classroom context by conducting ethnographic interviews with eight Latino immigrant entrepreneurs recruited through a small business training program. The study found that examining investment alone was insufficient for understanding participant experience. A more comprehensive analysis indicated that each participant had a unique relationship with English, encompassing situated language use, past learning experiences, current investment in learning, and feelings about using English. Participants' relationships with English affected and were affected by the kinds of businesses they had, how they positioned themselves, and how they were positioned by others. Participants who positioned themselves as "not English speakers" nevertheless used nonspoken semiotic resources to become English users and thus access economic opportunities. These findings have implications for English language teachers, social service providers, employers, and researchers in the applied linguistics and Teachers of English to Speakers of Other Languages communities. Overall, relationship with English provides a framework to assess, describe, and support immigrants' language use and learning.